{"ATC Code":"G - Genito urinary system and sex hormones","Abbreviation":"","Aliases":["17-Methyltestosterone","Metandren","Android","Testred","Androsan","Androsten","Mesterone","Virilon","Dumogran","Masenone"],"Biological Half-Life":"6-8 hours","CAS":"58-18-4","CanonicalSMILES":"CC12CCC(=O)C=C1CCC3C2CCC4(C3CCC4(C)O)C","ChEBI":"CHEBI:27436","ChEMBL":"CHEMBL1395","ChemicalClasses":["steroid"],"Color/Form":"Crystals from hexane","Dosing Info":[],"Drug Indication":"Methyltestosterone is an anabolic steroid hormone used to treat men with a testosterone deficiency. It is also used in women to treat breast cancer, breast pain, swelling due to pregnancy, and with the addition of estrogen it can treat symptoms of menopause.","Drug Warnings":"Cholestatic hepatitis and jaundice and abnormal liver function test results may occur in patients receiving 17-alpha-alkylandrogens such as methyltestosterone. These adverse hepatic effects may occur at relatively low doses of the drug. Drug-induced jaundice usually is reversible following discontinuance of the drug. Methyltestosterone should be discontinued if cholestatic jaundice or hepatitis occurs, or if liver function test results become abnormal during therapy with the drug, and the etiology of these disorders should be determined. Peliosis of the liver and hepatic neoplasms, including hepatocellular carcinoma, have been reported rarely in patients receiving long-term administration of androgenic anabolic steroids. Peliosis of the liver can be a life-threatening or fatal complication of androgen therapy.","DrugClasses":["hormone"],"European Community (EC) Number":"200-366-3","FDA Pharmacological Classification":"V9EFU16ZIF","Flash Point":"41 °F","Human Drugs":"Human drug -\u003e Prescription","IUPACName":"(8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13,17-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one","InChI":"InChI=1S/C20H30O2/c1-18-9-6-14(21)12-13(18)4-5-15-16(18)7-10-19(2)17(15)8-11-20(19,3)22/h12,15-17,22H,4-11H2,1-3H3/t15-,16+,17+,18+,19+,20+/m1/s1","InChIKey":"GCKMFJBGXUYNAG-HLXURNFRSA-N","MeSH Pharmacological Classification":"These compounds stimulate anabolism and inhibit catabolism. They stimulate the development of muscle mass, strength, and power. (See all compounds classified as Anabolic Agents.)","Melting Point":"161-166 °C","MolecularFormula":"C\u003csub\u003e20\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e","MolecularWeight":"302.5 g/mol","Odor":"Odorless","Pharmacodynamics":"Testosterone is a steroid hormone from the androgen group. Testosterone is primarily secreted from the testes of males. In females, it is produced in the ovaries, adrenal glands and by conversion of adrostenedione in the periphery. It is the principal male sex hormone and an anabolic steroid. In both males and females, it plays key roles in health and well-being. Examples include enhanced libido, energy, immune function, and protection against osteoporosis. On average, the adult male body produces about twenty times the amount of testosterone than an adult female's body does.","Physical Description":"Solid","PubChemId":6010,"Record Description":["Methyltestosterone can cause developmental toxicity according to state or federal government labeling requirements.","Methyltestosterone is a 17beta-hydroxy steroid that is testosterone bearing a methyl group at the 17alpha position. It has a role as an antineoplastic agent, an anabolic agent and an androgen. It is a 3-oxo-Delta(4) steroid, a 17beta-hydroxy steroid and an enone. It is functionally related to a testosterone.","A synthetic anabolic steroid used for treating men with testosterone deficiency or similar androgen replacement therapies. Also, has antineoplastic properties and so has been used secondarily in women with advanced breast cancer. Methyltestosterone is a schedule III drug in the US.","Methyltestosterone is an Androgen. The mechanism of action of methyltestosterone is as an Androgen Receptor Agonist.","Methyltestosterone is a methylated synthetic androgen receptor agonist with anabolic effects. Methyltestosterone, mimicking testosterone, binds to cytosolic androgen receptors, and the subsequent nuclear transfer of the ligand-receptor complex induces transcription initiation of androgen responsive genes. The gene products are responsible for normal growth and development of male sex organs and secondary sex characteristics. The agent also causes retention of nitrogen, sodium, potassium, phosphorus, as well as calcium.","METHYLTESTOSTERONE is a small molecule drug with a maximum clinical trial phase of IV (across all indications) that was first approved in 1973 and has 3 approved and 1 investigational indication.","A synthetic anabolic steroid used for treating men with testosterone deficiency or similar androgen replacement therapies. Also, has antineoplastic properties and so has been used secondarily in women with advanced breast cancer. Methyltestosterone is a schedule III drug in the US.","A synthetic hormone used for androgen replacement therapy and as an hormonal antineoplastic agent (ANTINEOPLASTIC AGENTS, HORMONAL).","See also: Estrogens, esterified; methyltestosterone (component of).","Methyltestosterone can cause developmental toxicity according to state or federal government labeling requirements.","Methyltestosterone is a 17beta-hydroxy steroid that is testosterone bearing a methyl group at the 17alpha position. It has a role as an antineoplastic agent, an anabolic agent and an androgen. It is a 3-oxo-Delta(4) steroid, a 17beta-hydroxy steroid and an enone. It is functionally related to a testosterone."],"References":[{"name":"Wikipedia","url":"https://en.wikipedia.org/wiki/Methyltestosterone"},{"name":"Wikidata","url":"https://www.wikidata.org/wiki/Q421768"},{"name":"DrugBank","url":"https://go.drugbank.com/drugs/DB06710"},{"name":"PubChem","url":"https://pubchem.ncbi.nlm.nih.gov/compound/6010"},{"name":"ChemSpider","url":"https://www.chemspider.com/Chemical-Structure.5788.html"},{"name":"ChEMBL","url":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1395"},{"name":"ChEBI","url":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:27436"},{"name":"Common Chemistry","url":"https://commonchemistry.cas.org/detail?cas_rn=58-18-4"},{"name":"HMDB","url":"https://hmdb.ca/metabolites/HMDB0015655"},{"name":"KEGG","url":"https://www.kegg.jp/entry/C07198"},{"name":"UNII","url":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/V9EFU16ZIF"},{"name":"EPA DSSTox","url":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID1033664"}],"Solubility":"Soluble in alcohol, methanol, ether and other organic solvents; sparingly soluble in vegetable oil","Stability/Shelf Life":"Affected by light","StructureBase64":"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Uses":"Anabolic Steroids; Androgens, Synthetic; Antineoplastic Agents, Hormonal","Title":"Methyltestosterone","UNII":"V9EFU16ZIF","Wikidata":"Q421768","XLogP":3.4}